


The Christmas Miracle

by chaosgroupie



Category: Supernatural
Genre: Christmas, F/M, Happy Ending, Romance
Language: English
Status: Completed
Published: 2019-06-09
Updated: 2019-06-22
Packaged: 2020-04-23 14:37:00
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 12,055
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19153036
Author URL: https://archiveofourown.org/users/chaosgroupie/pseuds/chaosgroupie
Summary: Megan Winchell meets Sam Winchester in third grade. They become best friends, and she meets Dean, his older brother. Even though he is four years older than them, she also becomes best friends with him. Follow them on their journey from 1991 to 2018, as they become closer friends. Until Christmas 2018, when she makes a wish to be able to redo one day of her life.This is based on a Hallmark movie I saw 'Kristin's Chrismas Past.' It's a really cute movie, and I definitely recommend it.





	1. Chapter 1

September 1991

“Good morning, my love,” fingers ran through my hair, waking me gently. “Come on, pumpkin, it’s your first day of school. We’ve got to get ready to go.”

“Mommy,” I whined, “five more minutes.”

She swatted my ass and laughed, “No way, Megan. Get up, lazy bones. Your dress is on the back of the chair for your first day.” Her voice lowered, “I know you miss him, sweetheart, I do too. But your daddy wouldn’t want you to be sad on the first day.”

I choked back a sob, “I know, Mommy.” I opened my eyes and looked at my beautiful mother. With her shoulder-length curly brown hair and bright blue eyes, she was often spoken of in hushed tones by my old friends. But after my father died a few months ago, we had moved to Lawrence, Kansas for a fresh start.

“I’ll be down in the kitchen waiting, don’t take too long.”

I climbed out of bed and sighed. It was the first day of the third grade, in a new city, with new people. Because my mother worked, I had to take the bus. Just another thing that losing my father had made more difficult. The dress she picked out for me was pink and fluffy, two of my favorite things. I loved feeling like a princess. Even if it brought back sad memories of my dad calling me Princess.

After getting dressed, I grabbed my backpack and headed downstairs. My mom had my lunch pail all ready to go and a toaster waffle cooked and on a paper towel. I picked it up, grabbed the bag, and kissed her cheek, “I love you, Mommy.”

“I love you too, baby.” She looked at me with tears in her eyes, “You’re growing up so fast.” She tucked a lock of hair behind my ear, “Just don’t grow up too quick.”

“No promises,” I grinned and skipped out the door, running to catch my bus.

There were several others at the bus stop about a block from my house, but I just stood there separate from them. Even in the best of times, I had a hard time making friends. I just wasn’t the bubbly outgoing type that my mother wished I were. I much preferred cuddling up on my bed with a good book than playing with other kids my age.

The bus stopped and I climbed on, sitting down in the window seat. A tall, gangly, shaggy-haired boy sat down next to me. He turned to me and grinned, “Good morning.” I just looked at him, “Name’s Sam.”

I sighed, “Megan.”

“Are you new? I mean, I’ve been at this school since the beginning and I would remember if I had met you last year.” He blushed, “I just mean… It’s a small school. We’ve all grown up together, so…”

“Yeah, I’m new,” I turned and looked out the window, suddenly sad.

I think he could tell because he started babbling, “You have any brothers or sisters? I have one, a brother, Dean. He’s my older brother, in seventh grade. He’s really cool. I wish I had a little brother or sister, but my mom…” He paused, “It’s just my dad and Dean now.”

“I’m sorry,” I reached out and grabbed his hand. “It’s just me and my mom, no brothers or sisters. My dad di… he died a few months ago, cancer.”

“My mom died in a house fire, I was a baby.”

We were both on the verge of tears, talking about something that I had never talked about before, not even with my mom. So I plastered a big smile on my face and changed the subject, “So, when’s your birthday. Mine’s May 2nd.”

“No way,” his mouth dropped open. “Mine too. 1983?”

“Yup.”

“Sweet.”

We were in the same classroom, and since the seating was organized by last name, we were sitting right next to each other. His was Winchester, and mine was Winchell. At the end of the day, we were on the bus again, sitting next to each other.

Sam bumped his shoulder into mine, “So, you wanna hang out at my place after school? My dad is working at the shop. Dean will be there, but he’ll leave us alone.”

“My mom won’t be home for a while either,” I smiled. “Sure, we can hang out.”

Turns out, he lived two houses down from me. So I ran over, left a note for my mother and dropped off my backpack. When I rang the doorbell, a blonde haired boy answered the door. Taller than both me and Sam, he must have been his older brother.

“Heya, Princess,” he smirked. “You here for Sammy?”

I frowned, “I’m not a princess.”

“Well, you certainly look like one.” He gestured at me, “Come on, Princess, that pink dress screams little girl.”

I crossed my arms over my chest, “You’re rude.”

He threw back his head and laughed, “You’re alright, Princess.” He laid a hand on my shoulder, “Come in, Sammy’s out back.”

He led me through the house to the back door. When I saw Sam, I ran out to him. He had a baseball that he kept tossing up and down. “Hey, Sam.”

He tossed the ball my way and I caught it. “Megan,” his smile was contagious. He looked over to the door and his smile fell a little, “I see you met Dean.”

“Yeah, your brother is something.” I looked back over at Dean before focusing solely on Sam, “Should we invite him to join us?”

“I don’t know,” he tossed the ball from hand to hand. “Dean is not much of a… joiner.”

“Alright,” I shrugged. “Well, toss it here.”

Later that night, I was sitting at the table eating macaroni and cheese with my mom. “Mommy, I made a friend today.”

“Really?” her eyebrows rose, but she had a huge smile on her face. “What’s her name? What’s she like?”

My face flushed, “His name is Sam. He lives two doors down from us.”

“A boy?” her voice rose.

“It’s not like that, mommy.” I huffed, “He’s just a friend.”

“Of course, pumpkin.” She grabbed my hand, “I’m just teasing you.”

“Do you think we could go and buy some new clothes?”

“What’s wrong with what you have?”

I knew my mother would never believe that I just wanted to change my style. Truthfully, I loved my dresses and pretty pink things, but what Dean had said to me really struck a chord. When my father had called me Princess, I loved it. But when he died, a part of me died with him. Dean called me Princess and it brought back a flood of memories, all good, but it still hurt.

“I just…” a tear rolled down my cheek. “It reminds me too much of daddy.”

“Oh, baby.” She stood and pulled me into her arms, “I’m so sorry, honey. We can go right now if you want.”

The next day, I wore a pair of jeans and a faded Led Zeppelin t-shirt. When Sam got on the bus next to me, he gave me a weird look, “What happened?”

I couldn’t tell him the truth. That Dean had said something to me that made me want to change. Instead, I just shrugged and lied, “It was too girly. I just wanted a change.”

He tugged at the sleeve of my shirt, “I liked the dress, it was pretty.” When I shrugged again, he forced a smile, “You know, Dean loves Led Zeppelin.”

It was my turn to be surprised, “Really? I just like the graphic. Never heard any of their music.”

“Don’t tell Dean. He’ll make you listen to their albums all day long,” he laughed. “Dad loves older music, calls it ‘classic.’ Dean picked it up from him.”

“Maybe we should invite him to hang out with us.” Sam glared at me, “It’s just, he’s your brother.”

He sighed, “You’re right. But if he says no, don’t blame me.”

After school, I did the same thing as the day prior. Dropped off my backpack at home and left a note for my mother. This time, when Dean answered the door he looked shocked, “Hey Princess, didn’t expect to see you out of your royal garb.”

I glared at him, “And to think, I was gonna ask if you wanted to play ball with us today.”

“No pouting, Princess.” He ruffled my hair, “I like the new look. It suits you.” As we walked outside, he threw his arm around me, “So, what’s your favorite Led Zeppelin song?”

May 1992

“Come on, mommy. We’re gonna be late.” I was wearing a pair of shorts and an AC/DC shirt with the sleeves cut off. Because the sleeve holes were too big, my mother made me wear a tank top underneath. “I want to get to Sam’s.”

“Honey, are you sure about this?”

“Mommy, we talked about this. Sam is my best friend. We share a birthday. I just want to spend it with my best friends.”

“Friends?” she gave me a weird look. “I thought it was just going to be Sam, Dean, and his father.”

“Dean’s my friend,” I turned defensive, knowing my mother wasn’t sure about him. “He’s my best friend too, mommy.”

“Honey…”

“No, mommy. Dean is a nice guy. I know he’s older than us, but he’s just lonely.”

“Oh, honey,” she crouched in front of me, holding my shoulders. “Alright, let’s go.”

John Winchester answered the door, “Megan.” He looked at my mother, “And you must be Megan’s mother.”

She stuck out her hand and shook his, “Teresa. Nice to meet you.”

“Mommy, I’m gonna go find Sam and Dean.”

“Alright, honey. Go have fun.”

They were in the backyard, throwing a baseball around. Dean saw me and a huge grin crossed his face, “Princess, you made it.” He ran over and picked me up in a hug, twirling me around. I couldn’t help but laugh. “How’s my little sister doing on her birthday?”

When he put me down, I laughed again, “This is so much better than a party.”

“Hey, where I am, the party follows.”

Sam came over and gave me a hug, “Happy birthday, Megan.”

“Happy birthday, Sam.”

“Alright, now that you kids got that out of the way,” Dean threw an arm around each of us. “Let’s play ball.”


	2. Chapter 2

March 1997

“Come on, Sammy,” I poked my best friend in the arm.

“It’s Sam,” he groaned. “You’re just as bad as Dean.”

“Well, he is my best friend too.”

“Sometimes I wish I’d never introduced you two,” he fell back onto his bed and threw his arm over his face.

“Please, Sammy.” When he glared at me, I corrected myself, “Please, Sam. We can sneak into the party, it’ll be fun. Dean’s always talking about how awesome these parties are.”

“Meg, we’re only thirteen. No one's gonna want us there.”

I smacked him in the arm, “You’re a spoilsport.” I put on my best puppy dog expression, “Pretty please with sugar on top.” I stuck out my lower lip and batted my eyelashes at him, “Let’s go to the party.”

“Fine.” He threw a pillow at me and I laughed, “We’ll go.”

I jumped on top of him and wrapped my arms around him, “I love you, Sammy.”

“I love you too, Meg. Now, let’s go to that party.”

Same as usual, I was wearing a pair of jeans and a vintage t-shirt. Dean had imposed his love of classic rock on me, and now I actually liked it. Sam didn’t understand, but it just brought Dean and me closer together. It was too bad that he was four grades ahead of me, otherwise, we would probably be closer friends. As it was, we didn’t see him that often because he had friends his own age. He was also a senior in high school, although he never pretended not to know us, even when his friends would rib him for talking to children.

We walked the three blocks to the party. When I opened the door to the front of the house, the music was loud and thumping. I grabbed Sam’s hand and we wove through the crowd. Surrounded by pretty girls in short skirts, Dean was sitting on the couch, one of the girls on his lap kissing him. Something tightened in my throat and I dropped Sam’s hand.

A girl came up and grabbed Sam. He turned to me, “I’m gonna go have some fun. Find me when you want to leave.”

“Yeah, yeah.” I headed over to where the drinks were, finding a bottle of cheap vodka. I grabbed it and took a big swig, coughing.

The music started playing one of my favorite Led Zeppelin songs. I took another large swig from the bottle and put it down, moving out to the open area in the living room where people were dancing. My hands lifted in the air, I moved my body from side to side to the beat of the music. Someone grabbed my hips from behind and started grinding against me. I was drunk enough that I didn’t really care.

Someone else started grinding from the front and I laughed. I knew I was right to come to the party. My first time drinking was going a lot better than I had expected. Suddenly, a hand moved the guy in front of me out of the way, “Can I cut in?”

A hard body pressed against my front as the one at my back left. Fingers tipped my head up, “What are you doing here, Princess?”

“Dean!!” I wrapped my arms around his neck. “This is so much fun.”

As I stumbled, Dean’s arms wrapped around me and he led me to the back of the house. Once we were in the backyard, he held me as he looked at me in concern, “What are you doing here? Your mother must be worried sick, wondering where you are.”

“We wanted to see what all the fuss was about,” my words were slurred. “I’m having so much fun.” I leaned against his body, enjoying his warmth.

He hugged me close and we stood like that for several minutes, quiet. Finally, he spoke, “Princess, who’s we?”

“Sammy came with me.”

He sighed. Lowering me into a chair, he crouched in front of me, “Wait here a moment, Princess. I’m going to tell Sammy that I’m taking you home.”

I leaned back staring at the stars. I must have fallen asleep because I woke up in Dean’s arms as carried me out of the house. My hand reached up and pressed against his cheek, “Hi.”

“Hi, Princess,” he smiled. “I’m taking you home.”

“No!” I struggled in his arms. “I don’t wanna go home.”

“Princess…”

“No!” I struggled enough that I fell out of his arms to the ground, “Ouch.”

“Maybe that will teach you to fight me.” He laughed and knelt on the ground, “You really don’t want to go home?” I shook my head, “Lucky for you, Sammy told me you were sleeping on the couch at our place tonight. Dad won’t care that you’ve been drinking.”

“Can we just… do something?” unsteady, I got to my feet before falling into Dean’s arms again.

“What do you want to do?” he led me over to the Impala, putting me in the passenger seat.

As he buckled me in, I smiled, “I just don’t want the night to end. I haven’t had this much fun in… forever.”

“Alright, Princess. I know a place.”

We drove to the edge of the city, a place I knew as the makeout spot. It overlooked the city, high on a hill. Dean pulled into the parking lot and got out before helping me out as well. He easily lifted me onto the hood of his car, then climbed up himself. We laid back and stared at the stars.

“Thanks, Dean.” I grabbed his hand with mine, interlacing our fingers.

“No worries, Princess. What are big brothers for?”

The little crush that I’ve been developing on Dean for years hurt to hear those words, but it didn’t diminish. He always treated me like I was one of the guys, especially since I changed my look. I just sighed, tightening my fingers, “I love you, Dean.”

“I love you too, Princess.” Even though he didn’t mean it the same way I did, it still made butterflies dance in my stomach.

I woke in Dean’s arms again as he carried me into the house. “Dee,” I said softly.

“Hey, Princess, we’re home.” He set me on my feet in the living room, “You feeling okay?”

I nodded and groaned as pain erupted behind my eyes, “Maybe not.” I fell onto the couch and covered my eyes with my hand, “Oh god, please tell me I didn’t do anything stupid.”

“No more than usual,” he joined me on the couch and wrapped an arm around me. I yawned, “You're tired. I should let you get some sleep.”

He tried to stand but I grabbed his arm, “Please, Dean, I don’t want to be alone.”

Sighing, he rubbed his eyes, “Well, I’m not sleeping on the couch.” He stood and pulled me up, “Come on, Princess. Let’s go to bed.”

The next morning, I woke up feeling overly warm and like something heavy was on top of me. When I opened my eyes, I saw a shirtless Dean wrapped around me. The blanket was half over us, so I couldn’t see if he was wearing anything on the bottom, but I could tell that I was still wearing my shirt and underwear.

I tried to pull out of his arms, but he moaned and pulled me close again, placing a kiss against my throat, “Five more minutes.”

As much as I wanted to stay in his bed, I knew that my Dean would never do that to me. I reached up a hand and shook him gently, “Dean, wake up.” He groaned again, “Please, Dean. Wake up.”

His eyes fluttered open and a look of shock crossed his face. He pulled away quickly and fell out of the bed, “What are you doing in my bed?”

“I don’t know,” my head was killing me. At least he was wearing boxers. “God, I’m never drinking again.”

“You’re thirteen, Princess, you shouldn’t have been drinking in the first place.” He stood and pulled on jeans and a shirt, “At least you came to the party I was at so I could take care of you.” He tossed me my pants, “You should probably get dressed and go find Sammy. He was worried about you last night.”

I got dressed and walked over to him, pulling Dean into a tight hug, “Thanks for taking care of me, Dean.”

“Of course, Princess,” he kissed the top of my head. “You’re my little sister. I would do anything for you.”


	3. Chapter 3

April 2001

My mom came in and woke me up, “Sweetheart, you need to get up so we can go buy your prom outfit.”

I rolled over, pulling the blanket over my head. “Mom,” I whined. “Can’t I just wear jeans or something?”

“No, Megan, you can’t just wear jeans.” She pulled the blanket off me, “Come on, it’s already noon. Get your skinny little ass up.”

“Fine,” I sighed and climbed out of bed. “I’ll be downstairs in five minutes.”

We ended up buying me a pair of black flowy slacks, and a black silk camisole that I was going to wear tucked in. Over the years, my style had gotten more tomboyish instead of less. I knew that my mother wasn’t very happy with that, but she never tried to get me to change. She probably thought that one day I would outgrow it. But I never did.

It was almost time for my date to show up and I was already dressed. I had a pair of sparkly black sandals and my mother's diamond necklace on. About two years after my father had died, she had turned her engagement ring into a pendant to wear. As she put it on me tonight, she told me that she wanted me to have it so I could always have a piece of my father with me.

Needless to say, I teared up and then spent the better part of ten minutes wiping my makeup off. I’m not even sure why I bothered putting any on. I never wore the stuff. I came downstairs and my mother had a look on her face, “Honey, Brian is on the phone for you.”

I went into the kitchen and she handed me the phone, “Hey Brian, what’s up?”

He coughed, “I’m sorry, Meg. I started getting sick yesterday and it’s only gotten worse. I’m not going to be able to go with you to the dance tonight.”

I sighed, “Don’t worry about it. I didn’t really want to go anyway. Get better quick.” I hung up the phone, trying not to look sad. 

My mother knew though. She came over, giving me a big hug, “I’m sorry, sweetheart. But hey, you’ll have Sam and Jessica.”

“No, it’s okay.” I picked up the phone and started dialing, “Let me just tell Sam.”

“Winchester residence, Dean speaking.”

“Hey, Dean,” I tried to keep the sadness from my voice.

He knew me too well though, “Princess, what’s wrong?”

“Can you put Sam on the phone?”

“He’s already left to get Jessica. What’s wrong, Princess? You know you can tell me anything.”

“My date to prom is sick. I was just calling to tell Sam that I wasn’t going.” My words were soft and thin, “Can you let him know?”

“Nonsense, you have to go to prom. This is the last one before you graduate.”

“I know, but…”

“No buts. I’ll be there in fifteen minutes.” He hung up the phone and I was left staring at the handset, wondering what in the hell was happening.

“Did you get in touch with him?”

“No, Dean answered.”

There must have been something in my voice because my mother took the phone from my hand and hung it up. “I don’t understand. What did he say?”

“He’s coming over.”

The doorbell rang. In a daze, I went to it and opened the door. Dean stood there, wearing his nicest jeans and a pink button-down shirt. He must have borrowed it from Sam because there is no way in hell that Dean Winchester would ever wear pink. He looked me up and down, then pulled a flower from behind his back, “You look beautiful, Princess.”

My face flushed as I took the flower that he must have picked from our neighbor's yard. “Thanks, Dean. You look pretty handsome yourself.” I touched the pink shirt, “You look good in this color.”

He flushed, “Sorry, my nice stuff is dirty. Had to borrow Sammy’s shirt.”

“Come on you two, let me take your picture.” My mother had a camera and a huge smile on her face. Dean wrapped his arm around my waist, and we smiled as she took a few photos. “You two look adorable.” My mother beckoned me over and handed me a small black purse. She whispered, “There’s some money inside in case you need it, and I put a condom in there as well.”

“Mom,” I gasped.

“Oh, honey,” she teared up, “my little girl is all grown up. Just be safe, okay? That’s why I’m giving you the condom. I know how you feel about Dean.”

I could feel my face turning bright red. I hissed, “We’re just friends.”

She raised an eyebrow, “Well, either way, you’re prepared.” She looked at Dean, “Take good care of her, Dean. And she doesn’t have a curfew, just please don’t drink and drive.”

“No worries, Mrs. Winchell. Megan is in good hands,” he held out his hand for me and I took it. “I’ll take excellent care of her.”

“I know you will.”

When we got in the car and started driving away, I laughed. Dean had to ask me twice what was so funny. “My… mother thinks… we’re going to have sex.”

Something flashed across his face for a quick second and then he laughed too, “Mothers. Can live with them…”

“Can’t live without them,” I finished. Dean put on some AC/DC and we drove to the school. When he pulled into the parking lot, I sighed. “Dean, will you hate me if I ask you to ditch prom with me. It’s just… I didn’t want to go to prom, but Sam was making me. Literally, the only reason I got a date was that he made his friend ask me.” I looked over at his blank face, “There is no one I would rather be there with than you, but this really isn’t my scene. And Dean, I don’t think it’s yours either.”

“You’re right.” He gave me a grin, “I was looking forward to dancing with you, though. And checking out all the hot chicks.”

“Eww, gross. You’re twenty-two Dean. All the girls that would be there are only eighteen. That seems a little young for you.”

“I’ll have you know I’m a young twenty-two, thank you very much,” he kept grinning. “Don’t worry, Princess, I wouldn’t really hit on one of your friends. I just think it’s adorable when your nose crinkles up in disgust.”

I punched him in the shoulder, “Can we just go to our spot? Hang out and watch the stars? I miss how we used to do that when we were younger.”

He started the car back up, “Sure thing, Princess. Anything for my little sis.”

I grimaced internally at those words. All jokes aside, my crush on Dean was no longer little. It had been at the party in eighth grade, but every time I saw him my insides tied into knots and I got tongue-tied. When my mother had given me the condom, my first thought was how I could convince Dean to sleep with me. However, my second thought was that I couldn’t do that to my best friend. He’d never thought of me that way, and I wasn’t about to lose him over something as stupid as a crush.

We got to the cliff and he parked the car. Before I could get out, he ran around the car and opened the door, holding it open with a small bow, “Madam, as requested.”

I laughed and gave him a hug, “You’re so good to me, Dean.” I had a thought, “You still have that Led Zeppelin tape, the one I gave you for your birthday a few years ago?”

“Of course,” he got back in the Impala, turned it on and popped in the tape. ‘Thank you’ started to play and I flushed. As it played, Dean came back around and gave me his hand, “Milady, may I have this dance?”

“Why, Mr. Winchester, I thought you would never ask.”

He pulled me into his arms, laughing. I wrapped my arms around his neck and stared up at him as the music played. 

_ If the sun refused to shine, _ __   
_ I would still be loving you. _ __   
_ When mountains crumble to the sea, _ _   
_ __ There will still be you and me.

_ Kind woman, I give you my all. _ _   
_ _ Kind woman, nothing more. _

_ Little drops of rain _ __   
_ Whisper of the pain. _ _   
_ __ Tears of love lost in the days gone by.

_ My love is strong, _ __   
_ With you there is no wrong. _ _   
_ __ Together we shall go until we die.

I felt myself starting to feel things that I had never felt before. In all the years that I’d known Dean, we had never been this close for this long. His body was pressed right against mine, his eyes staring right down into mine.

_ My, my, my. _

_ An inspiration's what you are to me. _ _   
_ _ Inspiration, look, see. _

_ And so today my world—it smiles, _ __   
_ Your hand in mine, we walk the miles, _ __   
_ Thanks to you it will be done, _ _   
_ __ For you to me are the only one.

_ Alright, yeah _

_ Happiness: no more be sad, _ _   
_ _ Happiness: I'm glad. _

_ If the sun refused to shine, _ __   
_ I would still be loving you. _ __   
_ Mountains crumble to the sea, _ _   
_ __ There will still be you and me.

When the song stopped, we stood there, wrapped in each other’s arms. I didn’t want to move, to break the spell. When Dean started to lower his head, I released him and back up. I think he must have realized what he had been about to do, because he looked embarrassed, “Thanks, Dean.” I took a step forward and placed a kiss on his cheek, “Now, how about we watch the stars?”

“Of course, Princess.” He turned off the car and we got up on the hood. After a few minutes, he grabbed my hand, threading his fingers with mine.

We lay there, hands intertwined for the better part of three hours. Neither of us said a word, we just stared at the cosmos. When I yawned, I turned toward him, “Dean?”

“Yes, Princess?”

“You know I love you, right?”

“Of course,” he grinned. “You know I love you too, right?”

My heart fluttered and I smiled, “I know.”

“You’re my little sister, for now, and for always,” he pulled me into his arms, and I rested my head on his shoulder. “I’m glad I could help make your prom a little better, even if we didn’t actually go.”

“This was a thousand times better.” 

**Notes for the Chapter:**

> It's going to be a few days before the next chapter, sorry. Writing two stories and working full time is a lot harder than it sounds.


	4. Chapter 4

May 2011

“Come on, Meg, it’s our twenty-eighth birthday. You should be having fun, not sitting in a corner moping.” Sam put his arm around me, making me feel tiny. At five foot seven, I wasn’t short, but next to this moose I was a midget.

I looked over to where Dean and Lisa were talking, my heart breaking. “I just don’t want to, Sam. Can’t a girl cry on her birthday without people making a big deal about it?”

“Sure, if it was anyone other than you.” He sat down at the barstool next to me and turned it, “What’s been going on with you lately? I mean, you’ve been down ever since New Year’s Eve when you introduced Dean and Lisa.” His eyes widened, “Are you upset because Dean is dating your coworker?”

“No, of course not,” the lie felt bitter on my tongue. I knew my face was flushed as well. I had never been a good liar, “Why would I be upset?” I looked over at them, “She’s perfect for him. Gorgeous, big boobs, slightly brain dead…”

“I don’t know, that’s why I am asking you.” He gave me a look, the one he used when questioning witnesses on the stand, “Seriously, what the fuck is going on with you? Before New Years, you were happy and bubbly. Then you introduce Dean to Lisa, they hit it off, and it’s like you’ve turned into a zombie. You don’t come out with us anymore, you don’t call or text. I even had to come and drag you out to your own birthday party. I know Dean misses you. I do too.”

“I’m sorry, Sammy.” I pressed my forehead against the edge of the bar as he rubbed my back, “I just… I didn’t realize it would hurt.”

“What?”

“Dean and Lisa.” I sat up and he gave me a questioning look. 

When I just stared at him, it was like a lightbulb had been turned on, “You like him, don’t you?” My face turned bright red, “Oh my god, you do. I always thought you had a little crush, but this… this is something more.” He chuckled, “Dean would get a kick out of this.”

I smacked him upside the head, “Don’t you dare, Sam Winchester. And it doesn’t matter anyway. Dean has only ever looked at me like a little sister, that’s it. So don’t you go and tell him something, or I’ll tell him that you’re the one that put a dent in his baby when we were learning to drive.”

“You wouldn’t?” he gasped.

“Wouldn’t I?” I grinned. “I took the fall because we both know that he wouldn’t beat me up because I’m a girl. But you, if he found out it was your fault, well nothing would protect you then.”

“That’s just cruel.” Sam laughed and pulled me into a hug, “Just talk to me next time okay? I know that it’s hard, liking someone you can’t have. I felt the same way when I first met Jessica and she was dating my friend Sean. But if you really like him, you should tell him. Because, Megan, he really likes Lisa. Like, really likes her. I think she might be it for him.”

“Well then, I definitely can’t mess it up.” I kissed his cheek, “Thanks for the talk. Now go back to your girlfriend. I’ll go wash up so it doesn’t look like I’ve been crying and come and join you.”

June 2015

There was a knock on my door. I opened it to see Dean standing there, a bottle of whiskey in his hand and a huge grin on his face. I let him in, shocked that he would show up at my apartment this late at night. “What are you doing here? Doesn’t Lisa want you home at a decent hour?”

He just fake glared at me, then laughed, “Come on, Princess. Have a drink with me. We’re celebrating.” He went into the kitchen, grabbed two cups, then forced me to sit on the couch with him. We drank our first shot and he turned to me, “She said yes!”

“Wait, what?” I was so confused.

“I’m getting married,” Dean sounded so excited, but inside my heart was breaking.

I forced a smile on my face, “I’m so happy for you.”

“Are you sure?” he looked concerned. Raising a finger, he touched the bridge of my nose, “Your nose is doing that thing you do when you lie. What’s wrong, Princess?”

I couldn’t tell him. Not the truth. I’d kept it hidden for so long, trying to fight my feelings for him. So he couldn’t tell I was lying, I put down my glass and pulled him into a hug, my face pressed against his chest. I gave him the best half-truth I could muster, “It’s just, I don’t get to see you as often anymore. And if you guys get married… next thing you know, you’ll have four kids and you’ll forget all about me.” 

“Princess, I’ll never forget you. You’ll always be my little sister, you know that.” He pushed me back slightly so he could look down at me, “I’ll make more time for you. I’m sorry. Lisa is just a little jealous. She keeps saying that you want more from me than friendship, and even though I know it’s not true, she gets mad when I spend time with you.”

Lisa knew! How the fuck did she know that I had feelings for Dean? I thought I could keep my feelings hidden, “I’m sorry.”

“Hey, don’t be sorry. You’re my best friend. I’ve known you now for twenty-five years. You’ve got Lisa beat, and always will. I knew you first.” He placed a kiss on my forehead, “Besides, you’re my sister. A guy's gotta keep in touch with family.”

“You know, I’m not actually your sister, right?” I asked sarcastically.

“Family don’t end with blood, Princess.” Letting me go, he poured us another drink, “Anyway, I have a question for you.”

“Shoot.”

We drank the shot and he gave me a hopeful look, “Will you be my best man?”

I coughed on the alcohol, “WHAT????” Coughing again, I looked at him curiously, “What about Sam?”

“I love Sammy, but I want you to stand with me. I would have made you the maid of honor, but Lisa is having her best friend do that.” He waggled his eyebrows, “Besides, I know you like pants better than skirts anyway.”

I sighed. Changing my style for Dean back when I was a kid, one of the dumbest decisions I’d ever made. Even though I have to admit, pants are way more comfortable than skirts, sometimes a girl just wants to feel like a girl. Not that Dean would ever look at me that way.

“Come on, Princess. What do you say?”

“Fine,” I sighed again. “Do I have to go to the strip club with you?”

His face fell, “Lisa doesn’t want me to go to one.” He plastered a smile on his face, “But that’s okay. I didn’t want to do that anyway. I was just thinking we could hit the Roadhouse. Have some burgers, some beers, play some pool…”

“Only you, Dean.” I nudged his shoulder, “But if you want to do the strip club thing… I would go with you. We could do it incognito one night. Lisa would never have to know.”

“That sounds awesome, but Lisa would know. Trust me.” His eyes went wide, “She’s got a creepy sixth sense about those sorts of things.”

August 2016

My outfit for the wedding was very similar to my prom outfit. A pair of dressy black slacks, a black silk camisole tucked in, and a pair of four-inch heels. My hair was up in a chignon, to make me look a little more masculine. Lisa was not happy that I was the best man, but since Dean had already asked me, there was nothing she could do about it.

“Dearly beloved, we are gathered here today to witness…”

The ceremony was long. Lisa was Catholic, so we ended up doing the entire traditional ceremony. I could tell that Dean was getting bored. He always shifted his weight from side to side when he was getting tired of doing something. Luckily for him, Lisa didn’t realize.

“If anyone has just cause for why these two should not wed, speak now or forever hold your peace.”

I just happened to be looking out at the audience when Sam’s eyes hit mine. He gave me a knowing glance and I glared at him. It may have been my dream to be with the man I love, but I knew that would never happen now. There was no way in hell I would ruin the best day of his life by professing my love now. If I was going to do it, I should have when he told me they were engaged.

“You may now kiss the bride.”

I had to hold back tears as they kissed. Lisa looked over the moon happy, Dean just looked relieved. I couldn’t figure out why he wasn’t happier to have just married the love of his life, but at least he wasn’t upset.

When we got to the party, the first thing I did was go to the bar, give the bartender $100 and bought a bottle of whiskey that I just drank out of straight. Once Lisa noticed, she glared at me, but then looked away. Apparently, she wasn’t going to let me spoil her big day.

I was trashed by the time the first dance happened. I knew I would need to be. She got to put her arms around him now, not me. She was going to be the last girl he kissed, not me. I started crying and put the whiskey bottle down, standing and leaving the hall.

Sam stopped me in the hallway as I was about to leave. “Megan…”

“Just leave it alone, Sammy,” my words came out garbled from being drunk and sobbing. “I should have known that I wouldn’t have been able to handle it today.”

“Why didn’t you just tell him?”

I whirled around, letting him see the tears that streaked down my cheeks, “Are you fucking kidding me? How exactly do you propose I should have done it?” I held my hands together, saying sarcastically, “Dean, I know you think of my like the little sister you never had, but I love you.” Then in a deeper voice, “Princess, you’re my little sister, you know I don’t think of you like that.”

Sam’s voice was soft and pitying, “You know he only calls you that to distance himself.”

“Fuck you, Sam.” My tears dried as I got angry, “You don’t know that. I’ve been his little sister for as long as I can remember. I’m one of the guys. He asked me to be his best man, for fuck's sake. I can never have him.”

“Megan,” he tried again. “I’m sorry.”

“Don’t be sorry.” I sighed and fell into his waiting embrace, “I’m sorry. You’re right. I should have told him sooner how I felt, but it’s too late now. I just have to pretend that I am not desperately in love with a guy that I can’t have.”

I cried in Sam’s arms for several minutes. A deep voice pulled me out of my sobbing, “Princess?”

Pulling away from Sam, I rubbed my eyes, trying to hide the tears, “Hey, Dean.”

“What’s wrong, Princess?”

I lied, “Nothing. Just had too much whiskey.” I winked at him, “You know how I get all emotional when I drink whiskey.”

“Princess…” he didn’t sound like he believed me. “Are you sure you’re okay?”

“Never better.” I gave him a quick hug, “Now get back to your… wife. I’m sure she’s missing you.”


	5. Chapter 5

December 2018

I answered the door, coffee in hand. Sam and Dean were there, holding presents and grinning. Or at least, Sam was grinning. Dean looked like someone had kicked his puppy. I opened the door and gestured for them to go inside, “Tree’s right over that way.”

None of us really wanted to go home for the holidays. We all lived in the same city, hours from our parents. They understood, happy that we had each other. We were celebrating at my place, because Lisa didn’t want to ‘mess’ up her house with decorations, and Jess had taken the kids to visit her parents for Christmas. Sam would have gone too, but he had a big case come up last minute and couldn’t go.

“It looks great, Megan,” Sam gave me a hug after setting down his presents. “Thanks for doing all this. Without the kids, Christmas is…”

“I know, Sammy.” I grinned when he glared at me, “Come on, Sammy, you know I’ll never change. Now, who wants eggnog.”

“It’s too early for alcohol.”

“Sam,” I crossed my arms over my chest. “It’s Christmas Eve. I’m here with my two favorite people in the whole world. If we want to have eggnog, then dammit, we’re going to have eggnog.”

Dean was being uncharacteristically quiet. Sam gave me a knowing look, “I’ll go grab it from the fridge.”

I pulled Dean over to the couch, forced him to sit, then sat next to him. Taking his hand in mine, I rubbed his palm, “What’s going on, Dean?”

He let out a shuddering breath, “Lisa cheated on me.”

“What the fuck?” I couldn’t help but yell. “Are you serious?”

He nodded, “Yeah. We were going through a rough patch, and I…” He closed his eyes, pressing on them to try and not cry, “I came home and found her in bed with someone she works with. I just don’t know what to do, Megan.”

This was bad. Dean never called me by his name, except when Lisa was around. Even when he was angry with me he still called me Princess. I started rubbing circles on his back, “Dean, honey, I’m so sorry. What can I do to help?”

“I don’t know.” He started to cry. Looking down at his lap, he attempted to hide the tears as they fell, “I love her. I don’t want to lose what we have.”

Sam came back into the room and I gave him a questioning glance. He just shrugged, “I know some good divorce attorneys in my office, I can get you their names if you want.”

“I just… I need to think about what I want to do.” Dean was quiet, “Do you think I can save my marriage?”

I wanted to tell him no. I wanted to tell him that she wasn’t good enough for him, but I didn’t do that. I ran my fingers through his hair, then pulled him against me, wrapping my arms around him tight, “I don’t know, Dean. But just know Sammy and I are here for you no matter what you decide.” I had an idea, “How would you like to do something we haven’t done for years?”

Sam raised his eyebrows, “And that would be…”

“Let’s go to Santa’s village. Sit on Santa’s lap, have a hayride, drink hot cocoa… the whole nine yards. It will help take your mind off things.” I continued rubbing his back as I sat there with his arms wrapped around me, “Maybe if you aren’t thinking about it, you can decide what you want to do.”

“Fine,” he pulled back and wiped at his eyes. “But I need some alcohol later if you’re going to make me spend the day with screaming children.”

We got to Santa’s village. We went on a hayride, Dean pouting the entire time. I drug him over to Santa, only to get told that adults couldn’t sit on his lap, but we could get pictures taken with him. Sam and Dean bowed out, but I went over, sitting next to Santa on the bench.

Santa looked at me, “So, little one, what would you like for Christmas?”

I sighed, trying to keep the melancholy look off my face, “What I want, you can’t give me.”

His eyes twinkled, “Try me. You don’t know unless you ask for it.”

Forcing a smile to my face so the boys wouldn’t realize something was wrong, I said, “I wish I could go back to before Dean fell in love with Lisa. I wish I could go back and tell him how I truly feel. That I’m in love with him and have been for years.”

“And why don’t you just tell him?” Santa’s sounded curious. “Wouldn’t that be the easiest solution?”

“Maybe.” I shrugged, “But he’s always thought of me as a little sister. And he loves his wife, even if they are having problems. I don’t want to be anyone's second choice.”

“Well, I can’t guarantee that my elves can make it happen,” he chuckled, “but, if you do go back to tell Dean that you love him, you will only have that one day. Until the stroke of midnight.”

“Like Cinderella?”

“Exactly.” He turned to face the camera, “Now, smile.”

I made myself smile before getting down. The grouchy woman manning the camera gave me a ticket, telling me the picture would be ready in a few minutes.

Sam came over, Dean a couple of steps behind him, “What were you doing with Santa for so long? I thought you were just going to take a picture.”

“He asked me what I wanted for Christmas.” I put a huge grin on my face, “I wished for a pony. Wonder if he’ll come through?”

Sam laughed, “Somehow, I don’t think so.”

When we made it back to my house, we all walked inside. I pulled Dean to the side, “Do you need to talk?” I could tell that he still seemed really upset, “We can go to my room, away from Sammy. You can tell me anything. I’m here for you.”

Dean forced a smile to his face. Looking down at me, he tucked a lock of hair behind my ear, “What would I do without you, Princess?” His smile fell and he took a deep breath, “I think I’m just going to go home. I need to talk to Lisa.”

“Are you divorcing her?” Sam asked, knowing exactly what I wanted to know. He probably wanted to know as well, “Because, seriously, I know several good divorce lawyers who would make sure you didn’t screwed.”

“I think I’m going to try and make it work with her.” He sighed, looking down at the ground, “Besides, there’s Ben to think about.”

“Ben’s not even yours Dean,” Sam was trying to be helpful, but Dean loved Ben almost as much as he would his own child.

“I’ve been the only man in that boy's life for seven years since I started dating Lisa. He is as much my son as hers,” Dean’s eyes grew dark as he glared at Sam. “You know how I feel about him.”

“I know, Dean. But you can’t keep yourself in a shit marriage just for the kid. You can stay in his life even if you guys aren’t together.”

“No,” Dean shook his head. “I’m going to tell Lisa that we need counseling. I love her, Sammy. I want to at least try to make it work without just giving up on her.” He turned to me, “Princess, I’m sorry Christmas Eve got ruined. Are we still welcome here tomorrow?”

“Of course, Dean,” I pulled him into a hug. “You guys are always welcome here. Lisa and Ben included.”

Dean left my house and Sam looked at me, “Are you okay?”

“I’ll be fine,” I let my fake smile fall. Sam knew that I was still in love with Dean, but he never pushed me on it anymore. “Just take your brother home. I’ll see you guys tomorrow.”

April 2001

“Fuck,” I groaned. The sun was streaming in my window, right into my eyes, so I pulled the blankets over my head. I should have known that nothing was going to happen by wishing for it. I sat up in bed and opened my eyes, taking in my old bedroom. The N’Sync posters on the wall brought me back to high school.

I closed my eyes and opened them again. Still there. I looked down and brought my hands up to my boobs. Yup, perky teenage boobs. Quickly, I climbed out of bed and went into my bathroom, looking in the mirror. A much younger version of me looked out from the mirror. It worked. Somehow.

I went downstairs, yawning. Taking a few minutes, I made some coffee, already missing my Keurig. Making coffee the old fashioned way just wasn’t as quick. When it finished, I poured myself a cup, added in some cream and sugar. As I took a big sip of coffee, my mother entered the room. 

“Megan?” she sounded so confused.

“Morning, Mom,” I turned around and gave her a big smile before taking another sip of my coffee.

“Are you drinking… coffee?”

“Yeah, I can’t help getting up early, but I need the caffeine to jolt myself to full consciousness.” Her mouth fell open in shock. I cringed, just realizing what I had said. “Don’t worry, mom. This is a one time deal. I just woke up early because I know there is a lot to get done today before prom.”

“The stores don’t open until ten, which is another,” she looked at the clock, “three hours from now.”

“I need to ask Sammy for a favor first. He’s always up this early getting his morning run in.”

“Alright,” she didn’t sound convinced but came over and poured herself a cup of coffee.

When I had finished mine, I rinsed it out and went upstairs. Quickly, I put on a pair of jeans and my favorite Led Zeppelin shirt. I missed this shirt so much. It would get destroyed about three years from now, causing me much anguish. But at least I got to see it one more time.

After I put on my sneakers, I ran over to the Winchester house and knocked on the door. Sam answered looking confused, “Megan? It’s before noon, what are you doing here?”

“I need two favors from you,” I gave him a huge smile. Sammy looked just as good at seventeen as he did at thirty-five.

“Sure,” he stepped back from the door. “Wanna come in?”

I shook my head, “No. So, my date is sick, or at least he’s going to call and tell me he’s sick in a few hours.”

“Wait, what?”

How to explain that I know the future without telling him that I know the future? “He seemed really sick yesterday. Told me that he might not make it. I’m assuming he’s going to cancel on me.”

“Okay,” Sam didn’t quite sound like he bought it, but I wasn't about to try harder to convince him. He would just think I was crazier than normal.

“So, first favor. I’m thinking that Dean will agree to be my date if I wait until the last minute to tell him. The only thing is, I’m pretty sure that his nice clothes won’t be clean.” I winked and grinned, “You know how Dean is with clothes. He only cleans them when necessary.”

“True.”

“Can you make sure that he’s got a clean pair of slacks and a shirt? I don’t want him to have to borrow something from you.”

“Of course,” Sam gave me a soft smile. “And I’m pretty sure you’re right. Dean went out with a girl a couple of weeks ago, only the one date, and he wore his only pair of pants and shirt. I’m fairly certain I saw them sitting on his bedroom floor.”

“Second favor. How would you like to come and help me pick out a dress for the dance?” This was a harder favor to ask for. The last time I wore a dress or even a skirt, was the first day we met. I wasn’t sure how he would take it, or if he would think there was something wrong with me.

Luckily, he didn’t think anything of it, “Sure. What time should I come over?”

Once the stores opened, Sam, my mother, and I went to look at dresses. It didn’t take long for me to find something that I liked. It was black and silky. A long sheath, thick enough that you couldn’t see through it, but thin enough that it felt decadent. A slit went halfway up the side of my thigh, the front dipped down a little, but the back was open nearly to the top of my ass. 

My mother didn’t want me to get a dress so revealing, but when Sam had stood there speechless for several minutes, she relented. She told me that if it made Sam, who was literally like a brother to me, speechless then my date wouldn’t be able to keep his eyes off me. We hadn’t told her that Dean was probably going to be taking me yet, but she wouldn’t care. She had always known about my little crush on him, ever since I was in middle school.

As I got ready for the night, I called Brian. His mother answered, “Hello?”

“Hi, Mrs. Anderson, it’s Megan. Is Brian still feeling sick?”

“Sick?” She yelled, “Brian, are you sick?” I didn’t hear what he said. She came back on, “Sorry sweetie, it sounds like he is. I’m sorry.”

“No worries. Just tell him to get better. My friend will be my backup.”

“I’ll let him know.”

After we hung up, I looked at the clock. It was about time for me to call Dean. My heart started to pound, I was terrified. What if this Dean said no? I took a deep breath. Of course, he wouldn’t say no. I dialed the number for the Winchester house, “Winchester residence, Dean speaking.”

“Hey, Dean.”

“What’s up, Princess?”

“So, my date for prom is sick.” I had thought briefly about trying to sound sad, but I didn’t want to manipulate him into going with me. “I was wondering if you would be willing to…”

“Of course I will, Princess.” He sounded cheerful, “Sammy even made me clean my nice clothes this morning for some reason. So, I have something to wear.”

I almost laughed, but contained it last second, “You are awesome, Dean Winchester.”

“I know, Princess. I know.” He laughed and I did as well, “I’ll be there in a little bit.”

I took the next few minutes to make sure my hair looked nice and put on some lip gloss. Even at thirty-five, I didn’t wear makeup, and I wasn’t about to start now. I slid on my sparkly sandals and clasped the diamond necklace that my mother had given me around my neck. I made myself a promise to wear it more often when I got back to my timeline. I had stopped wearing it, thinking it looked weird. But seeing it on my neck reminded me of my father, so I was going to wear it anyway.

The doorbell rang and I ran down the stairs, slowing as I saw Dean standing there. He was wearing a pair of charcoal slacks and a green button-down shirt that matched the color of his eyes. In his hands was a rose that I knew had come from our neighbor's yard.

His eyes raked me up and down. I saw him gulp, “Damn, Princess. You look… Fuck.”

I giggled, “Thanks, Dean.” I went over and gave him a hug, struggling not to shiver when his hands touched my bare back, “You look pretty fucking spectacular yourself.”

As I took the rose from him, I saw a look in his eyes I had never seen before. His pupils were large and he couldn’t stop looking down at my body. I flushed and turned away so I could put the rose into water. He groaned when he saw my back. Thankfully, my mother was in the other room.

I went out to the kitchen to find a vase. My mother was there, a wistful expression on her face. She handed me a small black purse I recognized as her going out purse, “There’s some money inside as well as condoms.”

“Mom,” I flushed. “I’m not sleeping with Dean.”

“It’s okay, honey. I know how much you like him.”

I groaned. As much as I wanted to fuck Dean, I wouldn’t do that to my teenage self. When she comes back to this body, I don’t want her confused as to why she’s no longer a virgin. “Mom, he’s my best friend, I’m not going to sleep with him.”

“Well, either way, it’s there if you need it.” She held up a camera, “Now, get out there so I can take your picture. You guys look so good, it would be a shame to not capture it on film.”

We went back out and I stood next to Dean. He wrapped his arm around my waist and I turned against him, one hand on his lower back the other on his chest. As I stared up at him, he stared down at me. The whole world fell away and all I wanted to do was kiss him. The camera made a noise, bringing me back to reality. 

I pulled away, “We should probably get going.” This time, I didn’t joke with him about my mother thinking we were going to have sex. However, I did still give him an out on the prom, “Dean, I know that prom isn’t your thing. To be honest, it’s not mine either. Do you maybe want to go hang out at our spot?”

“Princess, in that dress, we are going to prom for at least a little bit. I want everyone to see how fucking gorgeous you are.”

We ended up going to the dance for a couple of hours. The music was mostly fast, so I didn’t have to worry about spending too much time in Dean’s arms. Several girls tried to flirt with him, but he only had eyes for me. It made me feel like maybe he felt something for me. I knew that couldn’t be, however. I had no hope that telling him I was in love with him would make some big change in my life, but I wanted to make every second I spent with him memorable.

About an hour to midnight, we drove out to our spot on top of the cliff. He parked and we got out, sitting on the hood of his car. When I climbed up, my left leg was poking completely out of the dress, which rendered him speechless, again. I flushed but didn’t bother trying to hide it. I turned so I was facing him.

“Dean,” I reached my hand up and cupped his cheek. “Have I ever told you how much I value our friendship?”

“I already know. You’re my little…”

I put a finger on his lips, “Please don’t say I’m your little sister.” I closed my eyes and sighed, “I’m not sure I can take you calling me that again.”

He grabbed my hand and pulled it away from his face, “What are you talking about, Princess?”

My eyes flew open and I stared into his green eyes, “I need to tell you something, and I need you to listen to me.”

“Anything.”

Grabbing his hand, I interlaced our fingers together, “I’m not me. Not seventeen me, anyway.” His eyebrows rose, “This is going to sound crazy, but I’m from the future.”

His head fell back as he laughed loudly. “You can always figure out how to make me laugh.”

“I’m serious, Dean.” My voice was low, “Would the me you know wear this dress? Come on, Dean, you know me. The last time I wore a dress was the first day I met you. You have clean clothes because I knew that Brian was going to cancel on me. Also, I know things about you that you’ve never told me before. At least, not this version of me. How about when you lost your virginity?”

His face turned red, “There’s no way you know about that.”

It was my turn to laugh, “Oh, honey.” I patted his cheek, “It was on my twenty-first birthday. You and I were at a bar drinking shots to celebrate. We ended up back at my apartment, playing truth or dare. I asked you about losing your virginity. You told me all about the older woman, Rhonda. You were sixteen, she was eighteen. She had a thing for satin panties and had you wear a pair of pink ones. You got a little graphic about the sex, which I tried to put out of my memory. Because really, who wants to think about their best friend having sex? But the one thing I remember vividly is you telling me was how you kinda liked it.”

“What the fuck?” he pulled away from me and stood up. Dean started pacing back and forth, “How do you know that? I know for a fact I’ve never told you that story. I’ve never told anyone.”

I stood and put a hand on his arm, “Dean, that’s what I’m trying to tell you. Christmas 2018, I made a wish to be able to come back in time and tell you how I feel. Because in my time, I’ve lost you. I lost my chance with you and I wanted… no, I needed to tell you the truth before I lost you again.”

As he looked down at me, his eyes softened, “Princess, what do you mean?”

“God, how do I tell you?” My eyes went to the ground and he reached under my chin, tilting my head up, “Dean, I’ve been in love with you for years. I mean, future me has been in love with you for years. It all started in eighth grade at the party. I realized then that I had a crush on you. That just grew into something more. You are my best friend, my protector, the one guy in my life that I could always trust no matter what.”

“Princess…”

“No, Dean, I need to finish.” I sat back down on the car, smiling when he joined me. One more time, I threaded my fingers through his, “Now, I love Sammy to death. He’s my best friend too, but with him, it’s always been as a brother, nothing else. But Dean, we’ve known each other for twenty-seven years. It took me losing you to admit to myself how much I truly loved you.”

“Can I talk now?” I nodded and he reached up, tucking a lock of hair behind my ear, “I’m too old for you, sweetheart. No, don’t argue. You’re seventeen, at least, right now you are.”

“Dean, you’re only four years older than me. It’s not like you are an old man.”

“Sweetheart,” he cupped my cheek. “Let me finish. I care about you, so fucking much. I’ve known you for ten years. You’ve become more to me than just a friend. You know I love you, but…”

“You’re not in love with me.” I pulled away, wrapping my arms around my torso, “It’s okay. I knew it was a long shot.”

“Sweetheart… Megan, please look at me.” I just shook my head and he sighed, “If I’m being honest, since that party I’ve looked at you differently. I’ve tried not to, because honey, I’m four years older than you. It would have been illegal for me to do anything with you then. But you’re almost eighteen, or at least you will be next month. Do you really want to be with me?”

I turned back to him, “More than anything in the entire world.” I grabbed his face with both hands, pulling his face down toward mine. I placed a soft kiss on his lips. When he groaned and pulled me closer, deepening the kiss, my heart fluttered. I pulled back, “I only have until midnight, Dean. After that, I won’t remember any of this. I will be just like I was before, the same tomboy who has buried her crush so deep that she sets you up with the woman who you eventually marry.”

“Sweetheart,” he kissed me lightly. “Just tell me how I can make this work.”

“Christmas 2018. Can you wait for me? I know that’s a lot to ask. Asking you to wait seventeen years for me. It’s not fair to you.”

“Will it mean I get to be with you?” I nodded, “Sweetheart, I’ll wait forever for you.” He kissed me again, our tongues dancing against one another. I moaned into his mouth and he pulled away, chuckling, “You’re really good at that.”

“Well, remember I’m thirty-five, not really the seventeen-year-old virgin body I’m currently inhabiting.”

He choked, “Virgin?”

“Don’t worry, I take care of that in a couple of years. Some shitty boyfriend that you help me get over by getting me drunk.” Flipping his hand over, I traced patterns on his skin, “I need one other thing from you, Dean. Sam is getting into Stanford for law school. He’s going to become the best goddamn lawyer you’ve ever met. But your dad… he comes between you guys. Telling Sam that he’s a traitor for leaving. You don’t mean to, but it drives a wedge between you guys that doesn’t mend until after you get married. As much as I want you, I also want your relationship with Sam to stay strong.”

“He got into Stanford?” he sounded surprised.

“Well, he doesn’t know that yet, so don’t tell him.” I stood and pulled him up, wrapping my arms around his neck, “One last dance?”

He moved his hands to my waist, drawing me close, “As long as I get one last kiss.”

I stood on my toes and pressed my lips to his. It was relatively chaste compared the previous kisses, but nonetheless, it felt perfect.


	6. Chapter 6

December 2018

I woke at six, just as I always did. Turning over, I opened my eyes slowly, scared to see where I was. Everything looked just as I remembered it, I was in my apartment. I let out a sigh. Nothing had changed, which meant that it had only been a dream. A great dream, but a dream nonetheless.

I changed and went to the kitchen, making coffee for when everyone arrived. A couple of hours later, the doorbell rang. I answered it, surprised to see only Dean and Sam standing there. Dean had a couple of extra presents in his hands.

“Where are Lisa and Ben?” I asked.

Dean flushed and Sam gave me a confused look. When Sam turned to look at his brother, Dean just shook his head, “It’s just us today, Princess.”

I shrugged, “Okay.” I grabbed them coffees and then we sat down on the couch. Dean was holding onto the packages, almost as if he was afraid they would disappear. I sighed, “What’s going on? You seem a little… out of it.”

He handed me a thin, hard package, “I need you to open this first.”

I did as he asked. It was a picture frame with a picture of the two of us inside. The picture from prom, when I wore the silky dress. I looked up at him, mouth open in shock, “It wasn’t a dream.”

“No, sweetheart.” He smiled softly, “It wasn’t a dream.” Taking my hand, he took a second to collect his thoughts, “After that night, I was so excited and happy. The girl that I loved, well, she loved me back. But, as you said, you turned back into the girl you had been before. It took a while, but being around her made me think that I had made it all up in my head.”

“Dean…”

“No, sweetheart, I need to get this all out.” He closed his eyes for a second, “I’m not proud of the fact that I didn’t wait for you. You introduced me to Lisa and I fell for her. It wasn’t like what I felt for you, but you treated me like a brother so I figured I could have the next best thing.”

“I told you, Megan,” Sam interjected. “You should have told him how you felt years ago.”

“Shut up, Sammy,” we both said.

Dean chuckled, “After we married, I found out that Lisa was cheating on me. She had been since before we married. But I wanted to make it work. I didn’t want you or Sammy to know that I had fucked up by marrying her. Plus, she had Ben, and I loved… love that kid.” He tapped the frame, “But last year, your mother came over when I was visiting Dad and gave me that. She told me that I deserved to see how much you really loved me. That picture, it brought everything back and I hated myself for giving up. For giving up on us.”

“It may have been too late to say I waited for you, but Lisa and I have been divorced for months now, that’s why she’s not here.” He handed me the other package, “This one is from your mother. It’s your dress from prom. She thought you would need it to remember how you felt, but I knew after seeing the picture that you would already know.”

“Dean, I…”

He placed a finger on my lips, “Let me finish, sweetheart. I’m sorry I didn’t wait for you. But I need you to know that I never stopped loving you.” He climbed off the couch and got on his knee, “I know that we haven’t been on a date yet, but I know that you love me and I love you. We’ve both loved each other for years. We know each other's bad habits, the things that piss us off, and our favorite foods. We know each other better than most married couples do. Hell, we’ve been friends for twenty-seven years.”

Reaching into his pocket, he pulled out a ring, “If this is too soon, we can wait. But honestly, I don’t want to waste another minute of my life.” He slid it onto my finger, “Megan Winchell, my best friend, love of my life… will you marry me?”

I started crying and nodded, “Dean, I love you.”

He sat back on the couch and kissed me deeply, “I love you too, sweetheart.”

“Alright, now that the mushy stuff is out of the way,” Sam laughed as Dean and I glared at him. “What? It’s Christmas, I want to open my presents.”

**Notes for the Chapter:**

> I know this chapter is short. But as I said, this story was planned out to be short and fluffy. I wanted to end with them getting together, just as they do in the Hallmark movies that come out at Christmas time. End on a happy note. I hope you all enjoyed this story. I'm a sucker for happy endings.


End file.
